Dimethylformamide → 4-[2-(6-Benzyloxy-3-methyl-1H-indol-5-yl)-2-oxo-ethyl]-piperazine-1-carboxylic acid benzyl ester

HRID 1433162

Reaction equation

HRID 1433162 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:21](=[O:24])[CH2:22]Br)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[C:6]([CH3:25])=[CH:5]1)(=O)C.C([O-])([O-])=O.[K+].[K+].[C:32]([N:42]1[CH2:47][CH2:46]C[CH2:44][CH2:43]1)([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].C[N:49](C=O)C>>[CH2:35]([O:34][C:32]([N:42]1[CH2:43][CH2:44][N:49]([CH2:22][C:21]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][C:10]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:4][CH:5]=[C:6]3[CH3:25])=[O:24])[CH2:46][CH2:47]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 228749Benzyl piperidine-1-carboxylateHCID 579348421-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2-bromo-ethanone

Product 1

HCID 579348164-[2-(6-Benzyloxy-3-methyl-1H-indol-5-yl)-2-oxo-ethyl]-piperazine-1-carboxylic acid benzyl esterYield 17%

Procedure

Compound 1-(1-acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2-bromo-ethanone (0.039 g, 0.1 mmol), K2CO3 (0.019 g, 0.14 mmol) and Cbz-piperidine (0.026 ml, 0.1 mmol) was stirred in DMF (2 ml) at room temperature for 5 hours. The solvent was removed in vacuo and the residue redissolved in DCM and washed with water, brine, dried over MgSO4. Purification by column chromatography in hexane/EtOAc (3:2) afforded the product (0.008 g, 17%). LC/MS: RT=2.236 min. 498 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customPurification by column chromatography in hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-31d29dae79dc4d77b5a0dbc62178d1a6
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Linked notes

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